CT-ox | 1118943-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: CT-ox
• 英文别名: 2-methyl-[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)]-β-D-mannopyranosyl-(1->4)-1,2-dideoxy-α-D-glucopyranose]-[2,1-d]-oxazoline；(Galβ1->4GlcNAcβ1->2Manα1->6)[Galβ1->4GlcNAcβ1->2Manα1->3]Manβ1->4GlcNAc oxazoline；CT-GlcNAc oxazoline
• CAS: 1118943-57-9
• 化学式: C₅₄H₈₉N₃O₄₀
• 分子量: 1420.3
• InChiKey: HUJNGGXAGRRWBA-KZFGFNNASA-N

物化性质

• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -16.7
• 重原子数：
  97.0
• 可旋转键数：
  24.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  663.3
• 氢给体数：
  24.0
• 氢受体数：
  41.0

反应信息

• 作为反应物：
  描述：

  CT-ox 、 GlcNAc-LC-biotin 在 EndoM-N₁₇₅A 作用下， 反应 8.0h， 以72%的产率得到CT-GlcNAc2-LC-biotin
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Lectin Array Characterization of a Class of N-Glycan Clusters

  摘要：

  N-Glycans are major components of many glycoproteins. These sugar moieties are frequently involved in important physiological and disease processes via their interactions with a variety of glycan-binding proteins (GBP). Clustering effect is an important feature in many glycan-lectin interactions. We describe in this paper a chemoenzymatic synthesis of novel N-glycan clusters using a tandem endoglycosidase-catalyzed transglycosylation. It was found that the internal beta-1,2-linked GlcNAc moieties in the N-glycan core, once exposed in the nonreducing terminus, was able to serve as acceptors for transglycosylation catalyzed by Endo-A and EndoM-N175A. This efficient chemoenzymatic method allows a quick extension of the sugar chains to form a class of glycan clusters in which sugar residues are all connected by native glycosidic linkages found in natural N-glycans. In addition, a discriminative enzymatic reaction at the two GlcNAc residues could be fulfilled to afford novel hybrid clusters. Lectin microarray studies revealed unusual properties in glyco-epitope expression by this panel of structurally well-defined synthetic N-glycans. These new compounds are likely valuable for functional glycomics studies to unveil new functions of both glycans and carbohydrate-binding proteins.

  DOI：

  10.1021/ja9078539
• 作为产物：
  描述：

  SGP 在 endo-N-acetylglucosaminidase from Mucor hiemalis 、 neuraminidase 、 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 aq. phosphate buffer 为溶剂， 生成 CT-ox
  参考文献：
  名称：

  用非天然唾液酸糖肽对IgG进行 一锅N糖基化改造，可实现糖位特异性和双重有效的抗体-药物偶联物†

  摘要：

  内切-S突变体催化的化学酶转糖基化是体外的强大工具治疗性抗体的糖工程。在本文中，我们报告了使用蛋黄唾液酸糖肽（SGP）底物进行糖锅赫赛汀的一锅化学酶法合成。通过将这种一锅法与带有叠氮基或炔烃标记的新型非天然SGP衍生物相结合，糖基特异性缀合可以开发新的抗体-药物缀合物（ADC）。通过SDS-PAGE，完整抗体或ADC质谱分析和PNGase-F酶切分析，成功实现了位点特异性ADC和半位点双重药物ADC并进行了表征。癌细胞的细胞毒性测定表明，这些ADC的小分子药物释放依赖于嵌入结构中的可裂解Val-Cit连接片段。

  DOI：

  10.1039/c6ob01751g

文献信息

• Glycopeptides of the V3 loop of gp120 and derivatives; preparation and applications as HIV-1 vaccines.
  申请人：UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE

  公开号：EP1738764A1

  公开（公告）日：2007-01-03

  A method of making a synthetic glycopeptide, by addition of a synthetic oligosaccharide oxazoline to a GlcNAc-containing peptide precursor in the presence of an enzyme selected from among Endo-A and Endo-M. In a specific implementation, the method is utilized to synthesize a trivalent V3-domain glycopeptide including three V3-domain glycopeptides on a scaffold, wherein the three V3-domain glycopeptides are arranged to mimic the V3 domain presentation in trimeric gp120. Such trivalent V3- domain glycopeptides can be utilized in a vaccine for the treatment or prevention of HIV-1 infection.

  一种合成糖肽的方法，通过在Endo-A和Endo-M中选择的酶的存在下，将合成的寡糖噁唑线加入含有GlcNAc的肽前体。在一个具体的实现中，该方法被用于合成三价V3区域糖肽，包括三个V3区域糖肽在支架上，其中三个V3区域糖肽被排列以模拟三聚体gp120中的V3区域呈现。这样的三价V3区域糖肽可以用于治疗或预防HIV-1感染的疫苗中。
• Efficient Glycosynthase Mutant Derived from Mucor hiemalis Endo-β-N-acetylglucosaminidase Capable of Transferring Oligosaccharide from Both Sugar Oxazoline and Natural N-Glycan
  作者：Midori Umekawa、Cishan Li、Takayuki Higashiyama、Wei Huang、Hisashi Ashida、Kenji Yamamoto、Lai-Xi Wang

  DOI：10.1074/jbc.m109.059832

  日期：2010.1

  transglycosidase-like activity with "natural" N-glycan as well. These results also implicated the significance of amide side chain in the asparagine 175 of Endo-M for promoting oxazoline transglycosylation in the second step of the catalysis. The highly efficient syntheses of glycopeptides/glycoproteins by N175Q combined with synthetic sugar oxazolines or natural N-glycan substrates were exemplified

  Endo-M 是一种来自 Mucor hiemalis 的内切-β-N-乙酰氨基葡萄糖苷酶，是一种 85 糖苷水解酶家族。这种酶的独特之处在于它可以将各种类型的 N-聚糖的寡糖整块转移到不同的受体上，从而通过酶促产生多种糖缀合物。在这项研究中，我们对 Endo-M 的关键催化天冬酰胺 175 进行了突变和动力学研究。我们已经表明，大多数 Asn-175 突变体的水解活性显着降低，但充当能够使用合成糖恶唑啉进行转糖基化的糖合酶。我们的结果证实了这种天冬酰胺残基在底物辅助催化的第一步中促进恶唑啉离子中间体形成的关键作用。有趣的是，与 N175A 相比，发现 N175Q 突变体具有显着增强的糖恶唑啉类糖合酶活性，以及​​“天然”N-聚糖的转糖苷酶样活性。这些结果还暗示了 Endo-M 的天冬酰胺 175 中的酰胺侧链在催化的第二步中促进恶唑啉转糖基化的重要性。举例说明了 N175Q 结合合成糖恶唑啉或天然
• Huang, Wei; Li, Cishan; Li, Bing, Journal of the American Chemical Society, 2009, vol. 131, p. 2214 - 2223
  作者：Huang, Wei、Li, Cishan、Li, Bing、Umekawa, Midori、Yamamoto, Kenji、et al.

  DOI：——

  日期：——